Synthesis 2002(6): 0757-0760
DOI: 10.1055/s-2002-25773
PAPER
© Georg Thieme Verlag Stuttgart · New York

Efficient Synthesis of Substituted Terphenyls by Suzuki Coupling Reaction [1]

Hélène Chaumeil*, Claude Le Drian, Albert Defoin
Laboratoire de Chimie Organique et Bio-organique, U.M.R. 7015, Ecole Nationale Supérieure de Chimie de Mulhouse, 3, rue Alfred Werner, 68093 Mulhouse Cedex, France
Fax: +33(3)89336860; e-Mail: h.chaumeil@uha.fr;
Further Information

Publication History

Received 26 November 2001
Publication Date:
26 April 2002 (online)

Abstract

The Suzuki cross-coupling reactions of phenyl-1,4-dibor­onic acid bis-pinacol ester with a range of aryl halides are reported. The reaction proceeded smoothly, even with sterically hindered aryl halides, to give symmetrical terphenyls often quantitatively.

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Chaumeil H., Le Drian C. 31ème séminaire Hors-Ville d’Automne and 21st Regio Symposium in Organic and Bioorganic chemistry, 16-20th September 2001, Champery, Switzerland.

    References

  • 2a Suzuki A. Pure Appl. Chem.  1985,  57:  1749 
  • 2b Heck RF. Palladium Reagents in Organic Syntheses   Academic Press; London: 1985. 
  • 2c Matteson DS. Tetrahedron  1989,  45:  1859 
  • 2d Martin AR. Yang Y. Acta Chem. Scand.  1993,  47:  221 
  • 2e Suzuki A. Pure Appl. Chem.  1994,  66:  213 
  • 2f Miyaura N. Suzuki A. Chem. Rev.  1995,  95:  2457 
  • 2g Tsuji J. Palladium Reagents and Catalysts   Wiley; Chichester: 1995. 
  • 2h Stanforth SP. Tetrahedron  1998,  54:  263 
  • 2i Suzuki A. J. Organomet. Chem.  1999,  147 
  • 3a Schlüter AD. J. Polym. Sci., Polym. Chem.  2001,  1533 ; and references cited therein
  • 3b Synthesis of biaryls possessing three or four ortho-substituents by cross-coupling in the presence of Pd(PPh3)4: Miller RB. Dugar S. Organometallics  1984,  3:  1261 
  • 3c See also: Muller D. Fleury J.-P. Tetrahedron Lett.  1991,  32:  2229 
  • 3d See also: Fu J.-M. Zhao B.-P. Sharp MJ. Sniekus V. J. Org. Chem.  1991,  56:  1653 
  • 3e See also: Watanabe T. Miyaura N. Suzuki A. Synlett  1992,  207 
  • 3f See also: Zhang H. Xue F. Mak TCW. Chan K.-S. J. Org. Chem.  1996,  61:  8002 
  • 3g See also: Zhang H. Chan K.-S. Tetrahedron Lett.  1996,  37:  1043 
  • 3h See also: Anderson JC. Namli H. Roberts CA. Tetrahedron  1997,  53:  15123 
  • 3i See also: Jonhson MG. Foglesong RJ. Tetrahedron Lett.  1997,  38:  7001 
  • 3j See also: Zhang H. Kwong F.-Y. Tian Y. Chan K.-S. J. Org. Chem.  1998,  63:  6886 
  • 3k See also: Kamikawa T. Hayashi T. Tetrahedron  1999,  55:  3455 
  • 4a Thomson WJ. Gaudino J. J. Org. Chem.  1984,  49:  5237 
  • 4b Gronowitz S. Bobosik V. Lawitz K. Chem. Scr.  1984,  23:  120 
  • 4c Gronowitz S. Honfelt A.-B. Yang Y. Chem. Scr.  1988,  28:  281 
  • 4d Abraham MH. Grellier PL. The Chemistry of the Metal Carbon Bond   Hartley FR. Patai S. Wiley; New York: 1985. 
  • 5 Feuerstein M. Doucet H. Santelli M. Tetrahedron Lett.  2001,  42:  6667 ; and references cited therein
  • 6 Hoshino Y. Miyaura N. Suzuki A. Bull. Chem. Soc. Jpn.  1988,  61:  3008 
  • 7 Chaumeil H. Signorella S. Le Drian C. Tetrahedron  2000,  56:  9655 
  • 8a Danjo S, Saito T, Kadomachi H, and Kishimoto D. inventors; Japanese Patent  03250021.  1,4-bis(4-methoxyphenyl)benzene: 1991; Chem. Abstr. 1992, 116, 129935
  • 8b 1,4-bis(2-methylphenyl)benzene: Dowen M. Majewski S. Pettey D. Walker J. Wojcik R. Zorn C. Trans. Nucl. Sci.  1989,  36:  562 
  • 8c See also: De Vol TA. Wehe DK. Knoll GK. Nucl. Instrum. Methods Phys. Res., Sect. A  1994,  348:  156 
  • 8d See also: Ikoma Y, Taya F, and Naoi Y. inventors; Japanese Patent  0183030.  ; Chem. Abstr. 1989, 111, 153333
  • 8e Yamada S, and Tanabe S. inventors; Japanese Patent  07101900.  1,4-Bis(4-methoxyphenyl)benzene: ; Chem. Abstr. 1995, 123, 170537
  • 8f Linear optical materials, 1,4-bis(4-methoxyphenyl)benzene: Kauffman JM. Kelley CS. Ghiorghis A. Neister E. Seliskar CJ. Steppel RN. Proc. Int. Conf. Lasers  1989,  420 
  • 8g 1,4-Bis(2-methylphenyl)benzene: Golovkin SV. Konstantinchenko AA. Koslov VA. Kushnirenko AE. Pyschchev AI. Shershukov VM. Vasil’chenko VG. Zimyn KV. Nucl. Instrum. Methods Phys. Res,. Sect. A  1995,  362:  283 
  • 8h Kessler WJ, Davis SJ, Ferguson DR, and Pugh ER. inventors; US Patent  5610932. See also: ; Chem. Abstr. 1997, 126, 256922
  • 9a Banfi S. Montanari F. Pozzi G. Quici S. Tetrahedron  1994,  50:  9025 
  • 9b Houk KN. Menzer S. Newton SP. Raymo FM. Stoddart JF. Williams DJ. J. Am. Chem. Soc.  1999,  121:  1479 
  • 10a Todd MH. Balasubramanian S. Abell C. Tetrahedron Lett.  1997,  38:  6781 
  • 10b Schilling B. Kaufmann DE. Eur. J. Org. Chem.  1998,  701 
  • 10c Newnan MS. Hung W. J. Org. Chem.  1974,  39:  3950 
  • 10d Hart H. Harada K. Frank Du C.-J. J. Org. Chem.  1985,  50:  3104 
  • 10e Ikoma Y. Taya F. Ozaki E.-I. Higuchi S. Naoi Y. Fuji-i K. Synthesis  1990,  147 
  • 10f Ikoma Y. Ando K. Naoi Y. Akiyama T. Sugimori A. Synth. Commun.  1991,  481 
  • 11 Shoesmith JB. Mackie A. J. Am. Chem. Soc.  1928,  2338 
  • 12 Wirth HO. Königstein O. Kern W. Liebigs Ann. Chem.  1960,  634:  84 
  • 13 Mc Closkey CM. Coleman GH. Org. Synth. Coll. Vol. 3   Wiley; New York: 1955.  p.434 
  • 14 Kornblum N. Lurie AP. J. Am. Chem. Soc.  1959,  81:  2710 
  • 15 Cotton FA. Inorg. Synth.  1972,  13:  121 
  • 16 Uemura S. Tanaka S. Okamo RM. Hamana M. J. Org. Chem.  1983,  48:  3297 
  • 17a Coutts IGC. Goldschmid HR. Musgrave OC. J. Chem. Soc. C  1970,  488 
  • 17b Miller WT. Koch SD. J. Am. Chem. Soc.  1957,  79:  3081 
  • 18 Wasgindt M. Klemm E. Synth. Commun.  1999,  29:  103 
  • 19 Colonge J. Buendia J. Sabadie J. Bull. Soc. Chim. Fr.  1967,  4370 
  • 20 Prince CC. Mueller GP. J. Am. Chem. Soc.  1944,  66:  632 
  • 21a Böckmann K. Vögtle F. Liebigs Ann. Chem.  1981,  467 
  • 21b Wirth HO. Gönner KH. Stück R. Kern W. Makromol. Chem.  1963,  63:  30 
  • 22 Campbell TW. J. Am. Chem. Soc.  1960,  82:  3126 
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Chaumeil H., Le Drian C. 31ème séminaire Hors-Ville d’Automne and 21st Regio Symposium in Organic and Bioorganic chemistry, 16-20th September 2001, Champery, Switzerland.